Ring fused dihydropyrans, process for preparation and use thereof

ABSTRACT

The invention relates to compounds of the formula I                    
     in which the radicals R 1 , R 2 , R 3  and A have the meaning mentioned in the description. The invention further relates to a process for the preparation of the compounds of the formula I by means of solid-phase synthesis, and use thereof as pharmaceuticals.

This is a continuation of application Ser. No. 09/202,558 filed on Dec. 17 1998, now abandoned which is a 371 national stage filing of PCT/EP97/03146, filed Jun. 18, 1997, all of which are incorporated herein by reference.

The invention relates to compounds of the formula I

in which:

R¹ is

1. (C₁-C₁₄)-alkyl,

2. (C₂-C₆)-alkenyl,

3. (C₀-C₆)-alkyl-(C₃-C₁₀)-cycloalkyl-(C₀-C₆)-alkyl, where the alkyl moiety is optionally substituted by one or more OH groups,

4. (C₀-C₆)-alkyl-(C₆-C₁₄)-aryl,

5. (C₀-C₆)-alkyl-(C₃-C₉)-heteroaryl,

6. (C₂-C₆)-alkenyl-(C₆-C₁₄)-aryl,

7. (C₂-C₆)-alkenyl-(C₃-C₉)-heteroaryl,

8. (C₁-C₆)-alkanoyl,

9. a radical as defined under 4., 5., 6. or 7., where the (C₆-C₁₄)-aryl or (C₃-C₉)-heteroaryl moiety is substituted by 1, 2 or 3 identical or different radicals from the group consisting of (C₁-C₁₀)-alkyl, carboxyl, amino, nitro, (C₁-C₄)-alkylamino, hydroxyl, (C₁-C₄)-alkoxy, where one to all hydrogen atoms can be replaced by fluorine atoms, (C₆-C₁₂)-aryloxy, halogen, cyano, di-(C₁-C₄)-alkylamino, carbamoyl, sulfamoyl and (C₁-C₄)-alkoxycarbonyl, or two adjacent radicals on the (C₆-C₁₂)-aryl ring together are alkylenedioxy, preferably methylenedioxy;

R² is hydrogen, (C₁-C₁₀)-alkyl, (C₀-C₆)-alkyl-(C₆-C₁₂)-aryl or (C₀-C₆)-alkyl-(C₃-C₉)-heteroaryl, where the C₆-C₁₂-aryl or C₃-C₉-heteroaryl moiety is optionally substituted by 1, 2 or 3 identical or different radicals from the group consisting of carboxyl, amino, (C₁-C₄)-alkylamino, hydroxyl, (C₁-C₄)-alkoxy, halogen, cyano, di-(C₁-C₄)-alkylamino, carbamoyl, sulfamoyl and (C₁-C₄)-alkoxycarbonyl;

R³ is —X—R⁴;

X is —O—, —NR⁵— or —S—;

R⁴ is defined as R¹;

 where R⁴ together with R² can form a bridge member —CH₂—CH₂— or —CH₂—CH₂—CH₂—;

R⁵ is hydrogen or (C₁-C₆)-alkyl;

A is a fused cyclic ring system which

a) is substituted by one, two or three, preferably by one or two, oxo or hydroxyl functions, where one hydroxyl or oxo function is in the neighboring position to the dihydropyran ring, and

b) is mono, di- or polysubstituted, preferably mono- or disubstituted, by a (C₁-C₁₀)-alkyl radical or a carboxyl group, where at least one alkyl substituent carries a functional group, such as hydroxyl, carboxyl or amino;

and physiologically tolerable salts thereof.

Examples of fused cyclic ring systems A are 5- or 6-membered ring structures which can be aromatic or nonaromatic and can carry oxygen or nitrogen in the ring structure. Cyclopentane, cyclohexane, tetrahydrofuran, benzene, pyridine, imidazole, pyrazole, piperazine, dioxane and pyrimidine are particularly suitable.

(C₆-C₁₄)-Aryl is understood as meaning, for example, phenyl, naphthyl, anthracenyl or biphenyl.

Alkyl and radicals derived therefrom such as alkoxy can be straight-chain or branched. Halogen is preferably fluorine, chlorine or bromine.

A heteroaryl radical in the sense of the present invention is the radical of a monocyclic or bicyclic (C₃-C₉)-heteroaromatic, which contains one or two N atoms and/or an S or an O atom in the ring system. For the term “heteroaromatic” see Garrat, Vollhardt, Aromatizität [Aromaticity], Stuttgart 1973, pages 131-153. Examples of suitable heteroaryl radicals are the radicals of thiophene, furan, benzo[b]thiophene, benzofuran, pyrrole, imidazole, pyrazole, pyridine, pyrazine, pyrimidine, pyridazine, indole, quinoline, isoquinoline, oxazole, isoxazole, thiazole, isothiazole, isobenzofuran, indolizine, isoindole, indazole, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline and furazane.

Aryl, alkyl, heteroaryl and radicals derived therefrom can be mono- substituted or, if chemically possible, also polysubstituted as indicated above.

Functional groups such as hydroxyl, carboxyl or amino can also be provided with a customary chemical protective group.

Chiral centers, if not stated otherwise, can be present in the R or in the S configuration. The invention relates both to the optically pure compounds and to stereoisomer mixtures such as enantiomer mixtures and diastereomer mixtures.

The hydroxyl or oxo groups situated on the fused ring system A can be present in all tautomeric forms.

Possible salts are, in particular, alkali metal and alkaline earth metal salts, salts with physiologically tolerable amines and salts with inorganic or organic acids such as, for example, HCl, HBr, H₂SO₄, maleic acid or fumaric acid.

The compounds of the formula I described above are derivatives of dihydropyran, which can be synthesized rapidly, in an automated manner and in good yields on a solid support material (solid-phase synthesis) with the aid of combinatorial methods.

The compounds described above have a pharmacological action on various forms of disorder, such as metabolic disorders, e.g. diabetes and arteriosclerosis, on disorders of the cardiovascular system and of the central nervous system and on disorders of bone metabolism. They have immunomodulating properties and are suitable for the treatment of cancer and autoimmune disorders. An antiinfective action can moreover be observed.

Preferred compounds of the formula I are those in which

R¹ is (C₁-C₈)-alkyl, (C₀-C₆)-alkyl-(C₆-C₁₂)-aryl, (C₀-C₆)-alkyl-(C₃-C₉)-heteroaryl or (C₀-C₆)-alkyl-(C₆-C₁₂)-aryl, where the (C₆-C₁₂)-aryl moiety is substituted by 1, 2 or 3 identical or different radicals from the group consisting of (C₁-C₆)-alkyl, carboxyl, amino, nitro, hydroxyl, (C₁-C₆)-alkoxy, halogen or two adjacent radicals on the (C₆-C₁₂)-aryl ring are together methylenedioxy;

R² is hydrogen or (C₁-C₆)-alkyl, preferably hydrogen;

R³ is —X—R⁴;

X is —O—, NR or —S—;

R⁴ is (C₁-C₆)-alkyl which is optionally substituted by one or two radicals from the group consisting of OH, NR⁵; (C₀-C₆)-alkyl-(C₆-C₁₂)-aryl, preferably phenyl or benzyl; (C₃-C₆)-cycloalkyl or (C₁-C₆)-alkanoyl and

 where R⁴ together with R² can form a bridge member —CH₂—CH₂— or —CH₂—CH₂—CH₂—;

R⁵ is hydrogen or (C₁-C₆)-alkyl; and physiologically tolerable salts thereof.

Compounds of the formula I are further preferred in which R¹ is (C₁-C₆)-alkyl or (C₀-C₆)-alkyl-(C₆-C₁₂)-aryl, for example phenyl or benzyl. Compounds of the formula I are also preferred in which R² is hydrogen or (C₁-C₆)-alkyl, and also compounds of the formula I in which X is —O—.

Compounds of the formula I are further preferred in which the fused cyclic ring system A is 1,3-pyrimidine, benzene, dioxane or cyclohexane.

The synthesis is generally carried out by means of a suitable binding of cyclic 1,3-dicarbonyl compounds via a chemical linker to a polymeric matrix according to methods known to the person skilled in the art. Suitable polymeric matrices are, for example, polystyrene, polytetrafluoroethylene, polyacrylamide, which can optionally be extended with polyethylene chains (spacers) to improve the swellability. Suitable linker units are structures which specifically release the synthesized compound by means of acid, base, reduction, oxidation, by light or with fluoride ions, the linker unit remaining on the polymeric matrix (for a general survey of linker groups in solid-phase synthesis see J. Früchtel, G. Jung, Angew. Chemie Int. Ed. 1996, 35, 17-42).

The 1,3-dicarbonyl compounds linked to the polymer in such a way via a suitable functional group, such as —COOH, —OH, —NH₂, can be subjected to further customary reactions of organic chemistry. Synthesis on the solid phase in this case has the advantage that reagents and reactants can be used in a large excess, solvents can be widely varied and purification is effected by simple washing of the resin particles. After carrying out the synthesis stages sequentially, removal of the newly synthesized compounds is effected with the aid of specific reagents, according to the choice of linker (for a description of solid-phase synthesis see: J. Früchtel, G. Jung Angew. Chemie Int. Ed. 1996, 35, 17-42).

The solid-phase synthesis of ring-fused dihydropyran structures can be carried out by means of a tandem Knoevenagel-Diels-Alder reaction (L. F. Tietze et al, J. Heterocyclic Chemistry 1990, 27, 47f) (Scheme 1; Li=linker, P=polymeric matrix).

Preparation Process

A. Synthesis of polymer-bound 1,3-dioxocyclohexane-5-carboxylic acid

capacity: 0.5 mmol/g

1. Synthesis of (3)

60 g of the diketone (2) known from the literature are dissolved in 300 ml of dioxane abs. and 1 ml of conc. sulfuric acid is added. 54 ml of 2-trimethylsilylethanol are added and the mixture is allowed to react at room temperature for 24 h. After chromatography on silica gel, 38 g of (3) are obtained.

2. Synthesis of (5)

50 g of commercial 2-chlorotritylpolystyrene resin (Novabiochem), which is crosslinked with 2% divinylbenzene, are suspended in 300 ml of DMF and swollen over the course of 10 min. 11.0 g of (3) and 14.4 ml of N-ethylmorpholine are added. After 18 h at room temperature, the solution is separated off from the resin through a frit and the resin is washed thoroughly with DMF and methylene chloride. The resin is incubated with methanol over the course of 10 min and again washed thoroughly with DMF and methylene chloride. 60 g of (5) are obtained.

3. Synthesis of (4)

50 g of (5) are treated with 16.5 g of tetrabutylammonium fluoride (TBAF) and 300 ml of DMF abs. and shaken at room temperature for 4 h. The solution is filtered off with suction through a frit and the resin is washed thoroughly with DMF and methylene chloride. After drying in vacuo, 57 g of (4) are obtained. Removal of a sample with acetic acid yields (2) in 95% purity (HPLC, MS). The resin loading is determined as 0.5 mmol/g.

B. Synthesis of the cyclohexane- and benzene-fused dihydropyrans (scheme 2)

here, by way of example: R¹=n-hexyl, R²=H, R³=—O-tert-butyl

1. Synthesis of (3)

300 mg of (1) are preswollen in 0.2 ml of methylene chloride and treated with 60 μl of 1-heptanal and 2 ml of methanol. 10 mg of ethylene-diammonium diacetate are added and the mixture is allowed to react at room temperature for 2 h. 0.5 ml of tert-butyl vinyl ether is then added and the suspension is shaken at room temperature for a further 64 h. After removal of the solution through a frit, the resin is washed thoroughly with methylene chloride. After drying, about 330 mg of (3) remain. After removal of the polymer by treatment with acetic acidmethylene chloride and evaporation of the solvent, 3.4 mg of the free dihydropyran (3, Li-P=H) are obtained as a diastereomer mixture (HPLC/MS).

2. Synthesis of (4)

1 g of (3) is cooled to −70° C. in 6 ml of DMF abs. and 4 ml of THF abs. under argon. After addition of 2.5 ml of phosphazene P₄, the mixture is allowed to react at −70° C. of or 3 h. A solution of 191 mg of phenylselenyl chloride in 2 ml of THF abs. is then added, and the mixture is then allowed to react for 30 min at −70° C. and for 2 h at room temperature. It is then filtered off with suction using DMF and washed with buffer, pH 6, CH₃OH and MTB+toluene. The resin is removed overnight using 9:1 CH₂Cl₂/acetic acid at room temperature. 118 mg of (4) are obtained.

C. Synthesis of 1,3-dioxane-fused dihydropyrans (Scheme 3)

here by way of example with R¹=hexyl

1. Synthesis of the resin-bound Meldrum's acid derivative (3)

50 g of resin-bound 2-oxopentanecarboxylic acid (1) are swollen in 200 ml of acetic acid and treated with 20 g of malonic acid (2). 10 g of anhydrous ammonium acetate are added and the mixture is heated to 50° C. After stirring carefully for 3 h, the resin is freed from the solution, washed thoroughly with DMF and methylene chloride and dried. 53 g of (3) are obtained. Removal of a sample using anhydrous TFA yields the free Meldrum's. acid derivative (3, Li-P=H) (HPLC, MS).

2. Synthesis of (5)

1 g of (3), EDDA, 3 ml of CH₂Cl₂, 20 ml of CH₃OH abs. and 300 μl of n-heptanal are allowed to react at room temperature for 2 min. After addition of 3 ml of tert-butyl vinyl ether, the mixture is allowed to react at room temperature for 24 h. The resin is filtered off with suction and washed with DMF and MTB ether (5). The resin is removed at room temperature in 9:1 CH₂Cl₂/acetic acid over the course of 24 h, the mixture is filtered and the filtrate is evaporated.

D. 1,3-Pyrimidin-2-one-fused dihydropyrans can be synthesized, for example, according to the following scheme

1. Synthesis of (4)

About 200 mg of polymer-bound protected aminohexanecarboxylic acid (Novabiochem) are swollen in solvent (e.g. DMF) and treated with about 0.5 ml of piperidine. The mixture is stirred at room temperature for about 30 min, and the resin is freed from the solution and washed thoroughly with solvent (e.g. DMF). It is taken up again in solvent (e.g. 2 ml of DMF) and about 1 mmol of the isocyanate and about 0.3 ml of triethylamine are added. The mixture is stirred at room temperature for about 8 h. The resin is then freed from the solution and washed thoroughly with solvent (e.g. DMF and methylene chloride). After drying, (4) is obtained. The free urea derivative (4, Li-P=H) is obtained by removal of the linker.

2. Synthesis of (3)

About 200 mg of (4) are swollen in solvent in the cold (e.g. at 0° C. in DMF) and treated with about 1 mmol of monomethyl chloromalonate. About 0.5 ml of triethylamine is added and the mixture is stirred for about 2 h at 0° C. and for 1 h at a low heat (e.g. 50° C.). After washing the resin (3) is isolated. The free derivative of the N,N′-dialkylbarbituric acid (3, Li-P=H) is then obtained by removal of the linker.

3. Synthesis of (6) and (7)

About 300 mg of (3) are treated with about 0.5 mmol of the aldehyde and swollen in DMF. About 10 mg of ethylenediammonium diacetate and about 1 ml of methanol and also 1 ml of the enol ether are added and the mixture is stirred for about 8 h at low heat (e.g. 40° C.). After thorough washing of the resin with solvent (e.g. DMF and methylene chloride), it is dried. The removal of the trityl linker is carried out with acetic acid and methylene chloride. After concentration of the solvent in vacuo, the regio- and diastereomers (6) and (7) are obtained.

The invention further relates to pharmaceuticals which contain one or more compounds of the formula I according to the invention and/or their pharmacologically tolerable salts.

The pharmaceuticals are prepared by processes known per se, which are familiar to the person skilled in the art. As pharmaceuticals, the pharmacologically active compounds according to the invention (=active compound) are either employed as such, or preferably in combination with suitable pharmaceutical auxiliaries in the form of tablets, coated tablets, capsules, suppositories, emulsions, suspensions, granules, powders, solutions or preparations having protracted release of active compound, the active compound content advantageously being 0.1 to 95%.

The person skilled in the art is familiar on the basis of his/her expert knowledge with auxiliaries which are suitable for the desired pharmaceutical formulation. In addition to solvents, gel-forming agents, suppository bases, tablet auxiliaries and other active compound carriers, it is possible to use, for example, antioxidants, dispersants, emulsifiers, antifoams, flavor corrigents, preservatives, solubilizers or colorants.

The active compounds can be administered topically, orally, parenterally or intravenously, the preferred type of administration being dependent on the disease to be treated. Oral administration is preferred.

For an oral administration form, the active compounds are mixed with the additives suitable for this purpose such as excipients, stabilizers or inert diluents and brought by means of customary methods into suitable administration forms, such as tablets, coated tablets, hard capsules, aqueous, alcoholic or oily suspensions or aqueous, alcoholic or oily solutions. Inert excipients which can be used are, for example, gum arabic, magnesia, magnesium carbonate, potassium phosphate, lactose, glucose or starch, in particular cornstarch. In this case, preparation can be carried out both as dry and as moist granules. Suitable oily excipients or solvents are vegetable or animal oils, such as sunflower oil or fish liver oil.

For subcutaneous or intravenous administration, the active compounds or their physiologically tolerable salts, if desired with the substances customary for this purpose such as solubilizers, emulsifiers or other auxiliaries, are brought into solution, suspension or emulsion. Possible solvents are, for example, water, physiological saline solution or alcohols, e.g. ethanol, propanol, glycerol, and in addition also sugar solutions such as glucose or mannitol solutions, or alternatively a mixture of various solvents.

Suitable pharmaceutical preparations for topical and local use are eye drops which contain the active compound in aqueous or oily solution. For application to the nose, aerosols and sprays, and also coarse powders, which are administered by rapid inhalation through the nostrils, and especially nasal drops which contain the active compounds in aqueous or oily solution, are suitable.

The dose of the active compound of the formula I to be administered and the frequency of administration depend on the potency and duration of action of the compound according to the invention used; and additionally also on the nature and severity of the disease to be treated and on the sex, age, weight and individual responsiveness of the mammal to be treated. On average, the recommended daily dose of a compound according to the invention in the case of a mammal weighing approximately 75 kg—primarily a human—is in the range from approximately 10 to 500 mg, preferably from approximately 25 to 250 mg, where administration, if required, can take place in several doses per day.

The compounds listed in Tables 1-5 can be prepared according to the processes described above.

TABLE 1

Chem. Ex. R¹ mass  1 —CH₂—CH₂—CH₃ 280.32  2 4-Quinolyl 365.39  3 —CH₂—CH₂-phenyl 342.39  4 4-Methoxy-3-methylphenyl 358.39  5 4-Trifluoromethoxyphenyl 398.34  6 2,4,6-Trimethylphenyl 356.42  7 4-tert-Butylphenyl 370.45  8 3,5-Dimethoxyphenyl 374.39  9 —CH₂—C(CH₃)₃ 308.38 10 4-Ethylphenyl 342.39 11 Thiophen-2-yl 319.36 12 -Phenyl-CO₂—CH₃ 372.38 13 4-Phenoxyphenyl 406.44 14 —C(CH₃)═CH-phenyl-C(CH₃)₃ 410.51 15 —CH₂—CH(CH₃)-phenyl 356.42 16 —CH(CH₃)—CH(CH₃)—C₂H₅ 322.40 17 2,5-Dimethyl-4-methoxyphenyl 372.42 18 3,5-Dichloro-2-hydroxyphenyl 399.23 19 3,4-(Methylenedioxy)-6-nitrophenyl 403.35 20 3,5-Dimethoxy-2-methylphenyl 388.42 21 3-Ethoxy-4-methoxyphenyl 388.42 22 3-Ethoxy-4-phenylphenyl 420.46 23 —C₁₂H₂₅ 406.57 24 2,3-Dimethyl-4-methoxyphenyl 372.42 25 3-Hydroxy-4-nitrophenyl 375.34 26 2-Ethoxy-3,5-dimethoxyphenyl 418.45 27 3-Bromo-2,4-dimethoxyphenyl 453.29 28 2,4-Dimethoxy-3-phenyl 388.42 29 4-N—(C₄H₉)-2-phenyl 441.57 30 3-Bromo-3-methoxyphenyl 423.26 31 9-Anthracenyl 414.46 32 2-Hydroxy-3,5-diiodophenyl 582.13 33 3-Bromo-6-hydroxy-5-methoxyphenyl 439.26

TABLE 2

Chem. Ex. R¹ mass  1 —CH₂—CH₂—CH₃ 294.35  2 4-Quinolyl 379.41  3 —CH₂—CH₂-phenyl 356.42  4 4-Methoxy-3-methylphenyl 372.42  5 4-Trifluoromethoxyphenyl 412.36  6 2,4,6-Trimethylphenyl 370.45  7 4-tert-Butylphenyl 384.47  8 3,5-Dimethoxyphenyl 388.42  9 —CH₂—C(CH₃)₃ 322.40 10 4-Ethylphenyl 356.42 11 Thiophen-2-yl 333.39 12 -Phenyl-CO₂—CH₃ 386.40 13 4-Phenoxyphenyl 420.46 14 —C(CH₃)═CH-phenyl-C(CH₃)₃ 424.54 15 —CH₂—CH(CH₃)-phenyl 370.45 16 —CH(CH₃)—CH(CH₃)—C₂H₅ 336.43 17 2,5-Dimethyl-4-methoxyphenyl 386.45 18 3,5-Dichloro-2-hydroxyphenyl 413.26 19 3,4-(Methylenedioxy)-6-nitrophenyl 417.37 20 3,5-Dimethoxy-2-methylphenyl 402.45 21 3-Ethoxy-4-methoxyphenyl 402.45 22 3-Ethoxy-4-phenylphenyl 434.49 23 —C₁₂H₂₅ 420.59 24 2,3-Dimethyl-4-methoxyphenyl 386.45 25 3-Hydroxy-4-nitrophenyl 389.36 26 2-Ethoxy-3,5-dimethoxyphenyl 432.47 27 3-Bromo-2,4-dimethoxyphenyl 467.32 28 2,4-Dimethoxy-3-phenyl 402.45 29 4-N—(C₄H₉)-2-phenyl 455.60 30 3-Bromo-3-methoxyphenyl 437.29 31 9-Anthracenyl 428.49 32 2-Hydroxy-3,5-diiodophenyl 596.16 33 3-Bromo-6-hydroxy-5-methoxyphenyl 453.29

TABLE 3

R² = hydrogen Chem. Ex. R¹ R³ mass  1 —CH₂—CH₂—CH₃ Ethoxy 282.34  2 4-Quinolyl Ethoxy 367.40  3 —CH₂—CH₂-phenyl Ethoxy 344.41  4 4-Methoxy-3-methylphenyl Ethoxy 360.41  5 4-Trifluoromethoxyphenyl Ethoxy 400.35  6 2,4,6-Trimethylphenyl Ethoxy 358.44  7 4-tert-Butylphenyl Ethoxy 372.46  8 3,5-Dimethoxyphenyl Ethoxy 376.41  9 —CH₂—C(CH₃)₃ Ethoxy 310.39 10 4-Ethylphenyl Ethoxy 344.41 11 Thiophen-2-yl Ethoxy 321.38 12 -Phenyl-CO₂—CH₃ Ethoxy 374.39 13 4-Phenoxyphenyl Ethoxy 408.45 14 —C(CH₃)═CH-phenyl-C(CH₃)₃ Ethoxy 412.53 15 —CH₂—CH(CH₃)-phenyl Ethoxy 358.44 16 —CH(CH₃)—CH(CH₃)—C₂H₅ Ethoxy 324.42 17 2,5-Dimethyl-4-methoxy- Ethoxy 374.44 phenyl 18 3,5-Dichloro-2-hydroxyphenyl Ethoxy 401.24 19 3,4-(Methylenedioxy)-6-nitro- Ethoxy 405.36 phenyl 20 3,5-Dimethoxy-2-methyl- Ethoxy 390.44 phenyl 21 3-Ethoxy-4-methoxyphenyl Ethoxy 390.44 22 3-Ethoxy-4-phenylphenyl Ethoxy 422.48 23 —C₁₂H₂₅ Ethoxy 408.58 24 2,3-Dimethyl-4-methoxy- Ethoxy 374.44 phenyl 25 3-Hydroxy-4-nitrophenyl Ethoxy 377.35 26 2-Ethoxy-3,5-dimethoxy- Ethoxy 420.46 phenyl 27 3-Bromo-2,4-dimethoxy- Ethoxy 455.30 phenyl 28 2,4-Dimethoxy-3-phenyl Ethoxy 390.44 29 4-N—(C₄H₉)-2-phenyl Ethoxy 443.59 30 3-Bromo-3-methoxyphenyl Ethoxy 425.28 31 9-Anthracenyl Ethoxy 416.48 32 2-Hydroxy-3,5-diiodophenyl Ethoxy 584.15 33 3-Bromo-6-hydroxy-5- Ethoxy 441.28 methoxyphenyl 34 —CH₂—CH₂—CH₃ Phenylmercapto 346.45 35 4-Quinolyl Phenylmercapto 431.51 36 —CH₂—CH₂-phenyl Phenylmercapto 408.52 37 4-Methoxy-3-methylphenyl Phenylmercapto 424.52 38 4-Trifluoromethoxyphenyl Phenylmercapto 464.46 39 2,4,6-Trimethylphenyl Phenylmercapto 422.55 40 4-tert-Butylphenyl Phenylmercapto 436.57 41 3,5-Dimethoxyphenyl Phenylmercapto 440.52 42 —CH₂—C(CH₃)₃ Phenylmercapto 374.50 43 4-Ethylphenyl Phenylmercapto 408.52 44 Thiophen-2-yl Phenylmercapto 385.49 45 C₆H₄—CO₂—CH₃ Phenylmercapto 438.50 46 4-Phenoxyphenyl Phenylmercapto 472.56 47 —C(CH₃)═CH—C₆H₄—C(CH₃)₃ Phenylmercapto 476.64 48 —CH₂—CH(CH₃)—C₆H₅ Phenylmercapto 422.55 49 —CH(CH₃)—CH(CH₃)—C₂H₅ Phenylmercapto 388.53 50 2,5-Dimethyl-4-methoxy- Phenylmercapto 438.55 phenyl 51 3,5-Dichloro-2-hydroxyphenyl Phenylmercapto 465.36 52 3,4-(Methylenedioxy)-6-nitro- Phenylmercapto 469.47 phenyl 53 3,5-Dimethoxy-2-methyl- Phenylmercapto 454.55 phenyl 54 3-Ethoxy-4-methoxyphenyl Phenylmercapto 454.55 55 3-Ethoxy-4-phenylphenyl Phenylmercapto 486.59 56 —C₁₂H₂₅ Phenylmercapto 472.69 57 2,3-Dimethyl-4-methoxy- Phenylmercapto 438.55 phenyl 58 3-Hydroxy-4-nitrophenyl Phenylmercapto 441.46 59 2-Ethoxy-3,5-dimethoxy- Phenylmercapto 484.57 phenyl 60 3-Bromo-2,4-dimethoxy- Phenylmercapto 519.42 phenyl 61 2,4-Dimethoxy-3-phenyl Phenylmercapto 454.55 62 4-N—(C₄H₉)-2-phenyl Phenylmercapto 507.70 63 3-Bromo-3-methoxyphenyl Phenylmercapto 489.39 64 9-Anthracenyl Phenylmercapto 480.59 65 2-Hydroxy-3,5-diiodophenyl Phenylmercapto 648.26 66 3-Bromo-6-hydroxy-5- Phenylmercapto 505.39 methoxyphenyl 67 —CH₂—CH₂—CH₃ 2-Chloroethoxy 316.78 68 4-Quinolyl 2-Chloroethoxy 401.85 69 —CH₂—CH₂-phenyl 2-Chloroethoxy 378.85 70 4-Methoxy-3-methylphenyl 2-Chloroethoxy 394.85 71 4-Trifluoromethoxyphenyl 2-Chloroethoxy 434.80 72 2,4,6-Trimethylphenyl 2-Chloroethoxy 392.88 73 4-tert-Butylphenyl 2-Chloroethoxy 406.91 74 3,5-Dimethoxyphenyl 2-Chloroethoxy 410.85 75 —CH₂—C(CH₃)₃ 2-Chloroethoxy 344.84 76 4-Ethylphenyl 2-Chloroethoxy 378.85 77 Thiophen-2-yl 2-Chloroethoxy 355.82 78 -Phenyl-CO₂—CH₃ 2-Chloroethoxy 408.84 79 4-Phenoxyphenyl 2-Chloroethoxy 442.90 80 —C(CH₃)═CH-phenyl-C(CH₃)₃ 2-Chloroethoxy 446.97 81 —CH₂—CH(CH₃)-phenyl 2-Chloroethoxy 392.88 82 —CH(CH₃)—CH(CH₃)—C₂H₅ 2-Chloroethoxy 358.86 83 2,5-Dimethyl-4-methoxy- 2-Chloroethoxy 408.88 phenyl 84 3,5-Dichloro-2-hydroxyphenyl 2-Chloroethoxy 435.69 85 3,4-(Methylenedioxy)-6-nitro- 2-Chloroethoxy 439.81 phenyl 86 3,5-Dimethoxy-2-methyl- 2-Chloroethoxy 424.88 phenyl 87 3-Ethoxy-4-methoxyphenyl 2-Chloroethoxy 424.88 88 3-Ethoxy-4-phenylphenyl 2-Chloroethoxy 456.93 89 —C₁₂H₂₅ 2-Chloroethoxy 443.03 90 2,3-Dimethyl-4-methoxy- 2-Chloroethoxy 408.88 phenyl 91 3-Hydroxy-4-nitrophenyl 2-Chloroethoxy 411.80 92 2-Ethoxy-3,5-dimethoxy- 2-Chloroethoxy 454.91 phenyl 93 3-Bromo-2,4-dimethoxy- 2-Chloroethoxy 489.75 phenyl 94 2,4-Dimethoxy-3-phenyl 2-Chloroethoxy 424.88 95 4-N—(C₄H₉)-2-phenyl 2-Chloroethoxy 478.03 96 3-Bromo-3-methoxyphenyl 2-Chloroethoxy 459.72 97 9-Anthracenyl 2-Chloroethoxy 450.92 98 2-Hydroxy-3,5-diiodophenyl 2-Chloroethoxy 618.59 99 3-Bromo-6-hydroxy-5- 2-Chloroethoxy 475.72 methoxyphenyl 100  —CH₂—CH₂—CH₃ —O—CH₂—CH(CH₃)₂ 310.39 101  4-Quinolyl —O—CH₂—CH(CH₃)₂ 395.46 102  —CH₂—CH₂-phenyl —O—CH₂—CH(CH₃)₂ 372.46 103  4-Methoxy-3-methylphenyl —O—CH₂—CH(CH₃)₂ 388.46 104  4-Trifluoromethoxyphenyl —O—CH₂—CH(CH₃)₂ 428.41 105  2,4,6-Trimethylphenyl —O—CH₂—CH(CH₃)₂ 386.49 106  4-tert-Butylphenyl —O—CH₂—CH(CH₃)₂ 400.52 107  3,5-Dimethoxyphenyl —O—CH₂—CH(CH₃)₂ 404.46 108  —CH₂—C(CH₃)₃ —O—CH₂—CH(CH₃)₂ 338.45 109  4-Ethylphenyl —O—CH₂—CH(CH₃)₂ 372.46 110  Thiophen-2-yl —O—CH₂—CH(CH₃)₂ 349.43 111  -Phenyl-CO₂—CH₃ —O—CH₂—CH(CH₃)₂ 402.45 112  4-Phenoxyphenyl —O—CH₂—CH(CH₃)₂ 436.51 113  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—CH₂—CH(CH₃)₂ 440.58 114  —CH₂—CH(CH₃)-phenyl —O—CH₂—CH(CH₃)₂ 386.49 115  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—CH₂—CH(CH₃)₂ 352.47 116  2,5-Dimethyl-4-methoxy- —O—CH₂—CH(CH₃)₂ 402.49 phenyl 117  3,5-Dichloro-2-hydroxyphenyl —O—CH₂—CH(CH₃)₂ 429.30 118  3,4-(Methylenedioxy)-6-nitro- —O—CH₂—CH(CH₃)₂ 433.42 phenyl 119  3,5-Dimethoxy-2-methyl- —O—CH₂—CH(CH₃)₂ 418.49 phenyl 120  3-Ethoxy-4-methoxyphenyl —O—CH₂—CH(CH₃)₂ 418.49 121  3-Ethoxy-4-phenylphenyl —O—CH₂—CH(CH₃)₂ 450.53 122  —C₁₂H₂₅ —O—CH₂—CH(CH₃)₂ 436.63 123  2,3-Dimethyl-4-methoxy- —O—CH₂—CH(CH₃)₂ 402.49 phenyl 124  3-Hydroxy-4-nitrophenyl —O—CH₂—CH(CH₃)₂ 405.41 125  2-Ethoxy-3,5-dimethoxy- —O—CH₂—CH(CH₃)₂ 448.52 phenyl 126  3-Bromo-2,4-dimethoxy- —O—CH₂—CH(CH₃)₂ 483.36 phenyl 127  2,4-Dimethoxy-3-phenyl —O—CH₂—CH(CH₃)₂ 418.49 128  4-N—(C₄H₉)-2-phenyl —O—CH₂—CH(CH₃)₂ 471.64 129  3-Bromo-3-methoxyphenyl —O—CH₂—CH(CH₃)₂ 453.33 130  9-Anthracenyl —O—CH₂—CH(CH₃)₂ 444.53 131  2-Hydroxy-3,5-diiodophenyl —O—CH₂—CH(CH₃)₂ 612.20 132  3-Bromo-6-hydroxy-5- —O—CH₂—CH(CH₃)₂ 469.33 methoxyphenyl 133  —CH₂—CH₂—CH₃ n-Butyloxy 310.39 134  4-Quinolyl n-Butyloxy 395.46 135  —CH₂—CH₂-phenyl n-Butyloxy 372.46 136  4-Methoxy-3-methylphenyl n-Butyloxy 388.46 137  4-Trifluoromethoxyphenyl n-Butyloxy 428.41 138  2,4,6-Trimethylphenyl n-Butyloxy 386.49 139  4-tert-Butylphenyl n-Butyloxy 400.52 140  3,5-Dimethoxyphenyl n-Butyloxy 404.46 141  —CH₂—C(CH₃)₃ n-Butyloxy 338.45 142  4-Ethylphenyl n-Butyloxy 372.46 143  Thiophen-2-yl n-Butyloxy 349.43 144  -Phenyl-CO₂—CH₃ n-Butyloxy 402.45 145  4-Phenoxyphenyl n-Butyloxy 436.51 146  —C(CH₃)═CH-phenyl-C(CH₃)₃ n-Butyloxy 440.58 147  —CH₂—CH(CH₃)-phenyl n-Butyloxy 386.49 148  —CH(CH₃)—CH(CH₃)—C₂H₅ n-Butyloxy 352.47 149  2,5-Dimethyl-4-methoxy- n-Butyloxy 402.49 phenyl 150  3,5-Dichloro-2-hydroxyphenyl n-Butyloxy 429.30 151  3,4-(Methylenedioxy)-6-nitro- n-Butyloxy 433.42 phenyl 152  3,5-Dimethoxy-2-methyl- n-Butyloxy 418.49 phenyl 153  3-Ethoxy-4-methoxyphenyl n-Butyloxy 418.49 154  3-Ethoxy-4-phenylphenyl n-Butyloxy 450.53 155  —C₁₂H₂₅ n-Butyloxy 436.63 156  2,3-Dimethyl-4-methoxy- n-Butyloxy 402.49 phenyl 157  3-Hydroxy-4-nitrophenyl n-Butyloxy 405.41 158  2-Ethoxy-3,5-dimethoxy- n-Butyloxy 448.52 phenyl 159  3-Bromo-2,4-dimethoxy- n-Butyloxy 483.36 phenyl 160  2,4-Dimethoxy-3-phenyl n-Butyloxy 418.49 161  4-N—(C₄H₉)-2-phenyl n-Butyloxy 471.64 162  3-Bromo-3-methoxyphenyl n-Butyloxy 453.33 163  9-Anthracenyl n-Butyloxy 444.53 164  2-Hydroxy-3,5-diiodophenyl n-Butyloxy 612.20 165  3-Bromo-6-hydroxy-5- n-Butyloxy 469.33 methoxyphenyl 166  —CH₂—CH₂—CH₃ —O—(CH₂)₄—OH 326.39 167  4-Quinolyl —O—(CH₂)₄—OH 411.46 168  —CH₂—CH₂-phenyl —O—(CH₂)₄—OH 388.46 169  4-Methoxy-3-methylphenyl —O—(CH₂)₄—OH 404.46 170  4-Trifluoromethoxyphenyl —O—(CH₂)₄—OH 444.41 171  2,4,6-Trimethylphenyl —O—(CH₂)₄—OH 402.49 172  4-tert-Butylphenyl —O—(CH₂)₄—OH 416.52 173  3,5-Dimethoxyphenyl —O—(CH₂)₄—OH 420.46 174  —CH₂—C(CH₃)₃ —O—(CH₂)₄—OH 354.45 175  4-Ethylphenyl —O—(CH₂)₄—OH 388.46 176  Thiophen-2-yl —O—(CH₂)₄—OH 365.43 177  -Phenyl-CO₂—CH₃ —O—(CH₂)₄—OH 418.45 178  4-Phenoxyphenyl —O—(CH₂)₄—OH 452.51 179  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—(CH₂)₄—OH 456.58 180  —CH₂—CH(CH₃)-phenyl —O—(CH₂)₄—OH 402.49 181  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—(CH₂)₄—OH 368.47 182  2,5-Dimethyl-4-methoxy- —O—(CH₂)₄—OH 418.49 phenyl 183  3,5-Dichloro-2-hydroxyphenyl —O—(CH₂)₄—OH 445.30 184  3,4-(Methylenedioxy)-6-nitro- —O—(CH₂)₄—OH 449.42 phenyl 185  3,5-Dimethoxy-2-methyl- —O—(CH₂)₄—OH 434.49 phenyl 186  3-Ethoxy-4-methoxyphenyl —O—(CH₂)₄—OH 434.49 187  3-Ethoxy-4-phenylphenyl —O—(CH₂)₄—OH 466.53 188  —C₁₂H₂₅ —O—(CH₂)₄—OH 452.63 189  2,3-Dimethyl-4-methoxy- —O—(CH₂)₄—OH 418.49 phenyl 190  3-Hydroxy-4-nitrophenyl —O—(CH₂)₄—OH 421.41 191  2-Ethoxy-3,5-dimethoxy- —O—(CH₂)₄—OH 464.52 phenyl 192  3-Bromo-2,4-dimethoxy- —O—(CH₂)₄—OH 499.36 phenyl 193  2,4-Dimethoxy-3-phenyl —O—(CH₂)₄—OH 434.49 194  4-N—(C₄H₉)-2-phenyl —O—(CH₂)₄—OH 487.64 195  3-Bromo-3-methoxyphenyl —O—(CH₂)₄—OH 469.33 196  9-Anthracenyl —O—(CH₂)₄—OH 460.53 197  2-Hydroxy-3,5-diiodophenyl —O—(CH₂)₄—OH 628.20 198  3-Bromo-6-hydroxy-5- —O—(CH₂)₄—OH 485.33 methoxyphenyl 199  —CH₂—CH₂—CH₃ —O—(CH₂)₃—NH₂ 311.38 200  4-Quinolyl —O—(CH₂)₃—NH₂ 396.45 201  —CH₂—CH₂-phenyl —O—(CH₂)₃—NH₂ 373.45 202  4-Methoxy-3-methylphenyl —O—(CH₂)₃—NH₂ 389.45 203  4-Trifluoromethoxyphenyl —O—(CH₂)₃—NH₂ 429.40 204  2,4,6-Trimethylphenyl —O—(CH₂)₃—NH₂ 387.48 205  4-tert-Butylphenyl —O—(CH₂)₃—NH₂ 401.51 206  3,5-Dimethoxyphenyl —O—(CH₂)₃—NH₂ 405.45 207  —CH₂—C(CH₃)₃ —O—(CH₂)₃—NH₂ 339.43 208  4-Ethylphenyl —O—(CH₂)₃—NH₂ 373.45 209  Thiophen-2-yl —O—(CH₂)₃—NH₂ 350.42 210  -Phenyl-CO₂—CH₃ —O—(CH₂)₃—NH₂ 403.43 211  4-Phenoxyphenyl —O—(CH₂)₃—NH₂ 437.50 212  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—(CH₂)₃—NH₂ 441.57 213  —CH₂—CH(CH₃)-phenyl —O—(CH₂)₃—NH₂ 387.48 214  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—(CH₂)₃—NH₂ 353.46 215  2,5-Dimethyl-4-methoxy- —O—(CH₂)₃—NH₂ 403.48 phenyl 216  3,5-Dichloro-2-hydroxyphenyl —O—(CH₂)₃—NH₂ 430.29 217  3,4-(Methylenedioxy)-6-nitro- —O—(CH₂)₃—NH₂ 434.40 phenyl 218  3,5-Dimethoxy-2-methyl- —O—(CH₂)₃—NH₂ 419.48 phenyl 219  3-Ethoxy-4-methoxyphenyl —O—(CH₂)₃—NH₂ 419.48 220  3-Ethoxy-4-phenylphenyl —O—(CH₂)₃—NH₂ 451.52 221  —C₁₂H₂₅ —O—(CH₂)₃—NH₂ 437.62 222  2,3-Dimethyl-4-methoxy- —O—(CH₂)₃—NH₂ 403.48 phenyl 223  3-Hydroxy-4-nitrophenyl —O—(CH₂)₃—NH₂ 406.39 224  2-Ethoxy-3,5-dimethoxy- —O—(CH₂)₃—NH₂ 449.50 phenyl 225  3-Bromo-2,4-dimethoxy- —O—(CH₂)₃—NH₂ 484.35 phenyl 226  2,4-Dimethoxy-3-phenyl —O—(CH₂)₃—NH₂ 419.48 227  4-N—(C₄H₉)-2-phenyl —O—(CH₂)₃—NH₂ 472.63 228  3-Bromo-3-methoxyphenyl —O—(CH₂)₃—NH₂ 454.32 229  9-Anthracenyl —O—(CH₂)₃—NH₂ 445.52 230  2-Hydroxy-3,5-diiodophenyl —O—(CH₂)₃—NH₂ 613.19 231  3-Bromo-6-hydroxy-5- —O—(CH₂)₃—NH₂ 470.32 methoxyphenyl 232  —CH₂—CH₂—CH₃ —O-cyclohexyl 336.43 233  4-Quinolyl —O-cyclohexyl 421.50 234  —CH₂—CH₂-phenyl —O-cyclohexyl 398.50 235  4-Methoxy-3-methylphenyl —O-cyclohexyl 414.50 236  4-Trifluoromethoxyphenyl —O-cyclohexyl 454.45 237  2,4,6-Trimethylphenyl —O-cyclohexyl 412.53 238  4-tert-Butylphenyl —O-cyclohexyl 426.56 239  3,5-Dimethoxyphenyl —O-cyclohexyl 430.50 240  —CH₂—C(CH₃)₃ —O-cyclohexyl 364.48 241  4-Ethylphenyl —O-cyclohexyl 398.50 242  Thiophen-2-yl —O-cyclohexyl 375.47 243  C₆H₄—CO₂—CH₃ —O-cyclohexyl 428.48 244  4-Phenoxyphenyl —O-cyclohexyl 462.55 245  —C(CH₃)═CH—C₆H₄—C(CH₃)₃ —O-cyclohexyl 466.62 246  —CH₂—CH(CH₃)—C₆H₅ —O-cyclohexyl 412.53 247  —CH(CH₃)—CH(CH₃)—C₂H₅ —O-cyclohexyl 378.51 248  2,5-Dimethyl-4-methoxy- —O-cyclohexyl 428.53 phenyl 249  3,5-Dichloro-2-hydroxyphenyl —O-cyclohexyl 455.34 250  3,4-(Methylenedioxy)-6-nitro- —O-cyclohexyl 459.46 phenyl 251  3,5-Dimethoxy-2-methyl- —O-cyclohexyl 444.53 phenyl 252  3-Ethoxy-4-methoxyphenyl —O-cyclohexyl 444.53 253  3-Ethoxy-4-phenylphenyl —O-cyclohexyl 476.57 254  —C₁₂H₂₅ —O-cyclohexyl 462.67 255  2,3-Dimethyl-4-methoxy- —O-cyclohexyl 428.53 phenyl 256  3-Hydroxy-4-nitrophenyl —O-cyclohexyl 431.44 257  2-Ethoxy-3,5-dimethoxy- —O-cyclohexyl 474.55 phenyl 258  3-Bromo-2,4-dimethoxy- —O-cyclohexyl 509.40 phenyl 259  2,4-Dimethoxy-3-phenyl —O-cyclohexyl 444.53 260  4-N—(C₄H₉)-2-phenyl —O-cyclohexyl 497.68 261  3-Bromo-3-methoxyphenyl —O-cyclohexyl 479.37 262  9-Anthracenyl —O-cyclohexyl 470.57 263  2-Hydroxy-3,5-diiodophenyl —O-cyclohexyl 638.24 264  3-Bromo-6-hydroxy-5- —O-cyclohexyl 495.37 methoxyphenyl 265  —CH₂—CH₂—CH₃ —O—(CH₂)₆—OH 338.45 266  4-Quinolyl —O—(CH₂)₆—OH 423.51 267  —CH₂—CH₂-phenyl —O—(CH₂)₆—OH 400.52 268  4-Methoxy-3-methylphenyl —O—(CH₂)₆—OH 416.52 269  4-Trifluoromethoxyphenyl —O—(CH₂)₆—OH 456.46 270  2,4,6-Trimethylphenyl —O—(CH₂)₆—OH 414.54 271  4-tert-Butylphenyl —O—(CH₂)₆—OH 428.57 272  3,5-Dimethoxyphenyl —O—(CH₂)₆—OH 432.52 273  —CH₂—C(CH₃)₃ —O—(CH₂)₆—OH 366.50 274  4-Ethylphenyl —O—(CH₂)₆—OH 400.52 275  Thiophen-2-yl —O—(CH₂)₆—OH 377.48 276  -Phenyl-CO₂—CH₃ —O—(CH₂)₆—OH 430.50 277  4-Phenoxyphenyl —O—(CH₂)₆—OH 464.56 278  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—(CH₂)₆—OH 468.64 279  —CH₂—CH(CH₃)-phenyl —O—(CH₂)₆—OH 414.54 280  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—(CH₂)₆—OH 380.53 281  2,5-Dimethyl-4-methoxy- —O—(CH₂)₆—OH 430.54 phenyl 282  3,5-Dichloro-2-hydroxyphenyl —O—(CH₂)₆—OH 457.35 283  3,4-(Methylenedioxy)-6-nitro- —O—(CH₂)₆—OH 461.47 phenyl 284  3,5-Dimethoxy-2-methyl- —O—(CH₂)₆—OH 446.54 phenyl 285  3-Ethoxy-4-methoxyphenyl —O—(CH₂)₆—OH 446.54 286  3-Ethoxy-4-phenylphenyl —O—(CH₂)₆—OH 478.59 287  —C₁₂H₂₅ —O—(CH₂)₆—OH 464.69 288  2,3-Dimethyl-4-methoxy- —O—(CH₂)₆—OH 430.54 phenyl 289  3-Hydroxy-4-nitrophenyl —O—(CH₂)₆—OH 433.46 290  2-Ethoxy-3,5-dimethoxy- —O—(CH₂)₆—OH 476.57 phenyl 291  3-Bromo-2,4-dimethoxy- —O—(CH₂)₆—OH 511.41 phenyl 292  2,4-Dimethoxy-3-phenyl —O—(CH₂)₆—OH 446.54 293  4-N—(C₄H₉)-2-phenyl —O—(CH₂)₆—OH 499.69 294  3-Bromo-3-methoxyphenyl —O—(CH₂)₆—OH 481.39 295  9-Anthracenyl —O—(CH₂)₆—OH 472.58 296  2-Hydroxy-3,5-diiodophenyl —O—(CH₂)₆—OH 640.26 297  3-Bromo-6-hydroxy-5- —O—(CH₂)₆—OH 497.39 methoxyphenyl 298  —CH₂—CH₂—CH₃ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 366.50 299  4-Quinolyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 451.57 300  —CH₂—CH₂-phenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 428.57 301  4-Methoxy-3-methylphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 444.57 302  4-Trifluoromethoxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 484.52 303  2,4,6-Trimethylphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 442.60 304  4-tert-Butylphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 456.63 305  3,5-Dimethoxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 460.57 306  —CH₂—C(CH₃)₃ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 394.55 307  4-Ethylphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 428.57 308  Thiophen-2-yl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 405.54 309  -Phenyl-CO₂—CH₃ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 458.55 310  4-Phenoxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 492.62 311  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 496.69 312  —CH₂—CH(CH₃)-phenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 442.60 313  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 408.58 314  2,5-Dimethyl-4-methoxy- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 458.60 phenyl 315  3,5-Dichloro-2-hydroxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 485.41 316  3,4-(Methylenedioxy)-6-nitro- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 489.52 phenyl 317  3,5-Dimethoxy-2-methyl- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 474.60 phenyl 318  3-Ethoxy-4-methoxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 474.60 319  3-Ethoxy-4-phenylphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 506.64 320  —C₁₂H₂₅ —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 492.74 321  2,3-Dimethyl-4-methoxy- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 458.60 phenyl 322  3-Hydroxy-4-nitrophenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 461.51 323  2-Ethoxy-3,5-dimethoxy- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 504.62 phenyl 324  3-Bromo-2,4-dimethoxy- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 539.47 phenyl 325  2,4-Dimethoxy-3-phenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 474.60 326  4-N—(C₄H₉)₂-phenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 527.75 327  3-Bromo-3-methoxyphenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 509.44 328  9-Anthracenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 500.64 329  2-Hydroxy-3,5-diiodophenyl —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 668.31 330  3-Bromo-6-hydroxy-5- —O—CH₂—CH(C₂H₅)—(CH₂)₃—CH₃ 525.44 methoxyphenyl 331  —CH₂—CH₂—CH₃ t-Butyloxy 310.39 332  4-Quinolyl t-Butyloxy 395.46 333  —CH₂—CH₂-phenyl t-Butyloxy 372.46 334  4-Methoxy-3-methylphenyl t-Butyloxy 388.46 335  4-Trifluoromethoxyphenyl t-Butyloxy 428.41 336  2,4,6-Trimethylphenyl t-Butyloxy 386.49 337  4-tert-Butylphenyl t-Butyloxy 400.52 338  3,5-Dimethoxyphenyl t-Butyloxy 404.46 339  —CH₂—C(CH₃)₃ t-Butyloxy 338.45 340  4-Ethylphenyl t-Butyloxy 372.46 341  Thiophen-2-yl t-Butyloxy 349.43 342  -Phenyl-CO₂—CH₃ t-Butyloxy 402.45 343  4-Phenoxyphenyl t-Butyloxy 436.51 344  —C(CH₃)═CH-phenyl-C(CH₃)₃ t-Butyloxy 440.58 345  —CH₂—CH(CH₃)-phenyl t-Butyloxy 386.49 346  —CH(CH₃)—CH(CH₃)—C₂H₅ t-Butyloxy 352.47 347  2,5-Dimethyl-4-methoxy- t-Butyloxy 402.49 phenyl 348  3,5-Dichloro-2-hydroxyphenyl t-Butyloxy 429.30 349  3,4-(Methylenedioxy)-6-nitro- t-Butyloxy 433.42 phenyl 350  3,5-Dimethoxy-2-methyl- t-Butyloxy 418.49 phenyl 351  3-Ethoxy-4-methoxyphenyl t-Butyloxy 418.49 352  3-Ethoxy-4-phenylphenyl t-Butyloxy 450.53 353  —C₁₂H₂₅ t-Butyloxy 436.63 354  2,3-Dimethyl-4-methoxy- t-Butyloxy 402.49 phenyl 355  3-Hydroxy-4-nitrophenyl t-Butyloxy 405.41 356  2-Ethoxy-3,5-dimethoxy- t-Butyloxy 448.52 phenyl 357  3-Bromo-2,4-dimethoxy- t-Butyloxy 483.36 phenyl 358  2,4-Dimethoxy-3-phenyl t-Butyloxy 418.49 359  4-N—(C₄H₉)-2-phenyl t-Butyloxy 471.64 360  3-Bromo-3-methoxyphenyl t-Butyloxy 453.33 361  9-Anthracenyl t-Butyloxy 444.53 362  2-Hydroxy-3,5-diiodophenyl t-Butyloxy 612.20 363  3-Bromo-6-hydroxy-5- t-Butyloxy 469.33 methoxyphenyl 364  —CH₂—CH₂—CH₃ n-Propyloxy 296.37 365  4-Quinolyl n-Propyloxy 381.43 366  —CH₂—CH₂-phenyl n-Propyloxy 358.44 367  4-Methoxy-3-methylphenyl n-Propyloxy 374.44 368  4-Trifluoromethoxyphenyl n-Propyloxy 414.38 369  2,4,6-Trimethylphenyl n-Propyloxy 372.46 370  4-tert-Butylphenyl n-Propyloxy 386.49 371  3,5-Dimethoxyphenyl n-Propyloxy 390.44 372  —CH₂—C(CH₃)₃ n-Propyloxy 324.42 373  4-Ethylphenyl n-Propyloxy 358.44 374  Thiophen-2-yl n-Propyloxy 335.40 375  -Phenyl-CO₂—CH₃ n-Propyloxy 388.42 376  4-Phenoxyphenyl n-Propyloxy 422.48 377  —C(CH₃)═CH-phenyl-C(CH₃)₃ n-Propyloxy 426.56 378  —CH₂—CH(CH₃)-phenyl n-Propyloxy 372.46 379  —CH(CH₃)—CH(CH₃)—C₂H₅ n-Propyloxy 338.45 380  2,5-Dimethyl-4-methoxy- n-Propyloxy 388.46 phenyl 381  3,5-Dichloro-2-hydroxyphenyl n-Propyloxy 415.27 382  3,4-(Methylenedioxy)-6-nitro- n-Propyloxy 419.39 phenyl 383  3,5-Dimethoxy-2-methyl- n-Propyloxy 404.46 phenyl 384  3-Ethoxy-4-methoxyphenyl n-Propyloxy 404.46 385  3-Ethoxy-4-phenylphenyl n-Propyloxy 436.51 386  —C₁₂H₂₅ n-Propyloxy 422.61 387  2,3-Dimethyl-4-methoxy- n-Propyloxy 388.46 phenyl 388  3-Hydroxy-4-nitrophenyl n-Propyloxy 391.38 389  2-Ethoxy-3,5-dimethoxy- n-Propyloxy 434.49 phenyl 390  3-Bromo-2,4-dimethoxy- n-Propyloxy 469.33 phenyl 391  2,4-Dimethoxy-3-phenyl n-Propyloxy 404.46 392  4-N—(C₄H₉)₂-phenyl n-Propyloxy 457.61 393  3-Bromo-3-methoxyphenyl n-Propyloxy 439.31 394  9-Anthracenyl n-Propyloxy 430.50 395  2-Hydroxy-3,5-diiodophenyl n-Propyloxy 598.18 396  3-Bromo-6-hydroxy-5- n-Propyloxy 455.30 methoxyphenyl 397  —CH₂—CH₂—CH₃ Methoxy 268.31 398  4-Quinolyl Methoxy 353.38 399  —CH₂—CH₂-phenyl Methoxy 330.38 400  4-Methoxy-3-methylphenyl Methoxy 346.38 401  4-Trifluoromethoxyphenyl Methoxy 386.33 402  2,4,6-Trimethylphenyl Methoxy 344.41 403  4-tert-Butylphenyl Methoxy 358.44 404  3,5-Dimethoxyphenyl Methoxy 362.38 405  —CH₂—C(CH₃)₃ Methoxy 296.37 406  4-Ethylphenyl Methoxy 330.38 407  Thiophen-2-yl Methoxy 307.35 408  -Phenyl-CO₂—CH₃ Methoxy 360.37 409  4-Phenoxyphenyl Methoxy 394.43 410  —C(CH₃)═CH-phenyl-C(CH₃)₃ Methoxy 398.50 411  —CH₂—CH(CH₃)-phenyl Methoxy 344.41 412  —CH(CH₃)—CH(CH₃)—C₂H₅ Methoxy 310.39 413  2,5-Dimethyl-4-methoxy- Methoxy 360.41 phenyl 414  3,5-Dichloro-2-hydroxyphenyl Methoxy 387.22 415  3,4-(Methylenedioxy)-6-nitro- Methoxy 391.34 phenyl 416  3,5-Dimethoxy-2-methyl- Methoxy 376.41 phenyl 417  3-Ethoxy-4-methoxyphenyl Methoxy 376.41 418  3-Ethoxy-4-phenylphenyl Methoxy 408.45 419  —C₁₂H₂₅ Methoxy 394.55 420  2,3-Dimethyl-4-methoxy- Methoxy 360.41 phenyl 421  3-Hydroxy-4-nitrophenyl Methoxy 363.33 422  2-Ethoxy-3,5-dimethoxy- Methoxy 406.43 phenyl 423  3-Bromo-2,4-dimethoxy- Methoxy 441.28 phenyl 424  2,4-Dimethoxy-3-phenyl Methoxy 376.41 425  4-N—(C₄H₉)₂-phenyl Methoxy 429.56 426  3-Bromo-3-methoxyphenyl Methoxy 411.25 427  9-Anthracenyl Methoxy 402.45 428  2-Hydroxy-3,5-diiodophenyl Methoxy 570.12 429  3-Bromo-6-hydroxy-5- Methoxy 427.25 methoxyphenyl 430  —CH₂—CH₂—CH₃ —N(CH₃)—CO—CH₃ 309.36 431  4-Quinolyl —N(CH₃)—CO—CH₃ 394.43 432  —CH₂—CH₂-phenyl —N(CH₃)—CO—CH₃ 371.44 433  4-Methoxy-3-methylphenyl —N(CH₃)—CO—CH₃ 387.43 434  4-Trifluoromethoxyphenyl —N(CH₃)—CO—CH₃ 427.38 435  2,4,6-Trimethylphenyl —N(CH₃)—CO—CH₃ 385.46 436  4-tert-Butylphenyl —N(CH₃)—CO—CH₃ 399.49 437  3,5-Dimethoxyphenyl —N(CH₃)—CO—CH₃ 403.43 438  —CH₂—C(CH₃)₃ —N(CH₃)—CO—CH₃ 337.42 439  4-Ethylphenyl —N(CH₃)—CO—CH₃ 371.44 440  Thiophen-2-yl —N(CH₃)—CO—CH₃ 348.40 441  —C₆H₄—CO₂—CH₃ —N(CH₃)—CO—CH₃ 401.42 442  4-Phenoxyphenyl —N(CH₃)—CO—CH₃ 435.48 443  —C(CH₃)═CH—C₆H₄—C(CH₃)₃ —N(CH₃)—CO—CH₃ 439.55 444  —CH₂—CH(CH₃)—C₆H₅ —N(CH₃)—CO—CH₃ 385.46 445  —CH(CH₃)—CH(CH₃)—C₂H₅ —N(CH₃)—CO—CH₃ 351.44 446  2,5-Dimethyl-4-methoxy- —N(CH₃)—CO—CH₃ 401.46 phenyl 447  3,5-Dichloro-2-hydroxyphenyl —N(CH₃)—CO—CH₃ 428.27 448  3,4-(Methylenedioxy)-6-nitro- —N(CH₃)—CO—CH₃ 432.39 phenyl 449  3,5-Dimethoxy-2-methyl- —N(CH₃)—CO—CH₃ 417.46 phenyl 450  3-Ethoxy-4-methoxyphenyl —N(CH₃)—CO—CH₃ 417.46 451  3-Ethoxy-4-phenylphenyl —N(CH₃)—CO—CH₃ 449.51 452  —C₁₂H₂₅ —N(CH₃)—CO—CH₃ 435.61 453  2,3-Dimethyl-4-methoxy- —N(CH₃)—CO—CH₃ 401.46 phenyl 454  3-Hydroxy-4-nitrophenyl —N(CH₃)—CO—CH₃ 404.38 455  2-Ethoxy-3,5-dimethoxy- —N(CH₃)—CO—CH₃ 447.49 phenyl 456  3-Bromo-2,4-dimethoxy- —N(CH₃)—CO—CH₃ 482.33 phenyl 457  2,4-Dimethoxy-3-phenyl —N(CH₃)—CO—CH₃ 417.46 458  4-N—(C₄H₉)₂-phenyl —N(CH₃)—CO—CH₃ 470.61 459  3-Bromo-3-methoxyphenyl —N(CH₃)—CO—CH₃ 452.30 460  9-Anthracenyl —N(CH₃)—CO—CH₃ 443.50 461  2-Hydroxy-3,5-diiodophenyl —N(CH₃)—CO—CH₃ 611.17 462  3-Bromo-6-hydroxy-5- —N(CH₃)—CO—CH₃ 468.30 methoxyphenyl 463  —CH₂—CH₂—CH₃ —O—CH₂—CH₂—N—(C₂H₅)₂ 353.46 464  4-Quinolyl —O—CH₂—CH₂—N—(C₂H₅)₂ 438.53 465  —CH₂—CH₂-phenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 415.53 466  4-Methoxy-3-methylphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 431.53 467  4-Trifluoromethoxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 471.48 468  2,4,6-Trimethylphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 429.56 469  4-tert-Butylphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 443.59 470  3,5-Dimethoxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 447.53 471  —CH₂—C(CH₃)₃ —O—CH₂—CH₂—N—(C₂H₅)₂ 381.51 472  4-Ethylphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 415.53 473  Thiophen-2-yl —O—CH₂—CH₂—N—(C₂H₅)₂ 392.50 474  -Phenyl-CO₂—CH₃ —O—CH₂—CH₂—N—(C₂H₅)₂ 445.52 475  4-Phenoxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 479.58 476  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—CH₂—CH₂—N—(C₂H₅)₂ 483.65 477  —CH₂—CH(CH₃)-phenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 429.56 478  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—CH₂—CH₂—N—(C₂H₅)₂ 395.54 479  2,5-Dimethyl-4-methoxy- —O—CH₂—CH₂—N—(C₂H₅)₂ 445.56 phenyl 480  3,5-Dichloro-2-hydroxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 472.37 481  3,4-(Methylenedioxy)-6-nitro- —O—CH₂—CH₂—N—(C₂H₅)₂ 476.49 phenyl 482  3,5-Dimethoxy-2-methyl- —O—CH₂—CH₂—N—(C₂H₅)₂ 461.56 phenyl 483  3-Ethoxy-4-methoxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 461.56 484  3-Ethoxy-4-phenylphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 493.60 485  —C₁₂H₂₅ —O—CH₂—CH₂—N—(C₂H₅)₂ 479.70 486  2,3-Dimethyl-4-methoxy- —O—CH₂—CH₂—N—(C₂H₅)₂ 445.56 phenyl 487  3-Hydroxy-4-nitrophenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 448.48 488  2-Ethoxy-3,5-dimethoxy- —O—CH₂—CH₂—N—(C₂H₅)₂ 491.58 phenyl 489  3-Bromo-2,4-dimethoxy- —O—CH₂—CH₂—N—(C₂H₅)₂ 526.43 phenyl 490  2,4-Dimethoxy-3-phenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 461.56 491  4-N—(C₄H₉)₂-phenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 514.71 492  3-Bromo-3-methoxyphenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 496.40 493  9-Anthracenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 487.60 494  2-Hydroxy-3,5-diiodophenyl —O—CH₂—CH₂—N—(C₂H₅)₂ 655.27 495  3-Bromo-6-hydroxy-5- —O—CH₂—CH₂—N—(C₂H₅)₂ 512.40 methoxyphenyl 496  —CH₂—CH₂—CH₃ —O—CH₂-cyclohexyl-CH₂—OH 380.48 497  4-Quinolyl —O—CH₂-cyclohexyl-CH₂—OH 465.55 498  —CH₂—CH₂-phenyl —O—CH₂-cyclohexyl-CH₂—OH 442.55 499  4-Methoxy-3-methylphenyl —O—CH₂-cyclohexyl-CH₂—OH 458.55 500  4-Trifluoromethoxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 498.50 501  2,4,6-Trimethylphenyl —O—CH₂-cyclohexyl-CH₂—OH 456.58 502  4-tert-Butylphenyl —O—CH₂-cyclohexyl-CH₂—OH 470.61 503  3,5-Dimethoxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 474.55 504  —CH₂—C(CH₃)₃ —O—CH₂-cyclohexyl-CH₂—OH 408.54 505  4-Ethylphenyl —O—CH₂-cyclohexyl-CH₂—OH 442.55 506  Thiophen-2-yl —O—CH₂-cyclohexyl-CH₂—OH 419.52 507  -Phenyl-CO₂—CH₃ —O—CH₂-cyclohexyl-CH₂—OH 472.54 508  4-Phenoxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 506.60 509  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—CH₂-cyclohexyl-CH₂—OH 510.67 510  —CH₂—CH(CH₃)-phenyl —O—CH₂-cyclohexyl-CH₂—OH 456.58 511  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—CH₂-cyclohexyl-CH₂—OH 422.56 512  2,5-Dimethyl-4-methoxy- —O—CH₂-cyclohexyl-CH₂—OH 472.58 phenyl 513  3,5-Dichloro-2-hydroxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 499.39 514  3,4-(Methylenedioxy)-6-nitro- —O—CH₂-cyclohexyl-CH₂—OH 503.51 phenyl 515  3,5-Dimethoxy-2-methyl- —O—CH₂-cyclohexyl-CH₂—OH 488.58 phenyl 516  3-Ethoxy-4-methoxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 488.58 517  3-Ethoxy-4-phenylphenyl —O—CH₂-cyclohexyl-CH₂—OH 520.63 518  —C₁₂H₂₅ —O—CH₂-cyclohexyl-CH₂—OH 506.73 519  2,3-Dimethyl-4-methoxy- —O—CH₂-cyclohexyl-CH₂—OH 472.58 phenyl 520  3-Hydroxy-4-nitrophenyl —O—CH₂-cyclohexyl-CH₂—OH 475.50 521  2-Ethoxy-3,5-dimethoxy- —O—CH₂-cyclohexyl-CH₂—OH 518.61 phenyl 522  3-Bromo-2,4-dimethoxy- —O—CH₂-cyclohexyl-CH₂—OH 553.45 phenyl 523  2,4-Dimethoxy-3-phenyl —O—CH₂-cyclohexyl-CH₂—OH 488.58 524  4-N—(C₄H₉)₂-phenyl —O—CH₂-cyclohexyl-CH₂—OH 541.73 525  3-Bromo-3-methoxyphenyl —O—CH₂-cyclohexyl-CH₂—OH 523.42 526  9-Anthracenyl —O—CH₂-cyclohexyl-CH₂—OH 514.62 527  2-Hydroxy-3,5-diiodophenyl —O—CH₂-cyclohexyl-CH₂—OH 682.29 528  3-Bromo-6-hydroxy-5- —O—CH₂-cyclohexyl-CH₂—OH 539.42 methoxyphenyl 529  —CH₂—CH₂—CH₃ —O—C(CH₃)₂—CH₂—CH₃ 324.42 530  4-Quinolyl —O—C(CH₃)₂—CH₂—CH₃ 409.48 531  —CH₂—CH₂-phenyl —O—C(CH₃)₂—CH₂—CH₃ 386.49 532  4-Methoxy-3-methylphenyl —O—C(CH₃)₂—CH₂—CH₃ 402.49 533  4-Trifluoromethoxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 442.43 534  2,4,6-Trimethylphenyl —O—C(CH₃)₂—CH₂—CH₃ 400.52 535  4-tert-Butylphenyl —O—C(CH₃)₂—CH₂—CH₃ 414.54 536  3,5-Dimethoxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 418.49 537  —CH₂—C(CH₃)₃ —O—C(CH₃)₂—CH₂—CH₃ 352.47 538  4-Ethylphenyl —O—C(CH₃)₂—CH₂—CH₃ 386.49 539  Thiophen-2-yl —O—C(CH₃)₂—CH₂—CH₃ 363.46 540  -Phenyl-CO₂—CH₃ —O—C(CH₃)₂—CH₂—CH₃ 416.47 541  4-Phenoxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 450.53 542  —C(CH₃)═CH-phenyl-C(CH₃)₃ —O—C(CH₃)₂—CH₂—CH₃ 454.61 543  —CH₂—CH(CH₃)-phenyl —O—C(CH₃)₂—CH₂—CH₃ 400.52 544  —CH(CH₃)—CH(CH₃)—C₂H₅ —O—C(CH₃)₂—CH₂—CH₃ 366.50 545  2,5-Dimethyl-4-methoxy- —O—C(CH₃)₂—CH₂—CH₃ 416.52 phenyl 546  3,5-Dichloro-2-hydroxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 443.33 547  3,4-(Methylenedioxy)-6-nitro- —O—C(CH₃)₂—CH₂—CH₃ 447.44 phenyl 548  3,5-Dimethoxy-2-methyl- —O—C(CH₃)₂—CH₂—CH₃ 432.52 phenyl 549  3-Ethoxy-4-methoxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 432.52 550  3-Ethoxy-4-phenylphenyl —O—C(CH₃)₂—CH₂—CH₃ 464.56 551  —C₁₂H₂₅ —O—C(CH₃)₂—CH₂—CH₃ 450.66 552  2,3-Dimethyl-4-methoxy- —O—C(CH₃)₂—CH₂—CH₃ 416.52 phenyl 553  3-Hydroxy-4-nitrophenyl —O—C(CH₃)₂—CH₂—CH₃ 419.43 554  2-Ethoxy-3,5-dimethoxy- —O—C(CH₃)₂—CH₂—CH₃ 462.54 phenyl 555  3-Bromo-2,4-dimethoxy- —O—C(CH₃)₂—CH₂—CH₃ 497.39 phenyl 556  2,4-Dimethoxy-3-phenyl —O—C(CH₃)₂—CH₂—CH₃ 432.52 557  4-N—(C₄H₉)₂-phenyl —O—C(CH₃)₂—CH₂—CH₃ 485.67 558  3-Bromo-3-methoxyphenyl —O—C(CH₃)₂—CH₂—CH₃ 467.36 559  9-Anthracenyl —O—C(CH₃)₂—CH₂—CH₃ 458.56 560  2-Hydroxy-3,5-diiodophenyl —O—C(CH₃)₂—CH₂—CH₃ 626.23 561  3-Bromo-6-hydroxy-5- —O—C(CH₃)₂—CH₂—CH₃ 483.36 methoxyphenyl

TABLE 4

Ex. R¹ Chem. mass  1 —CH₃—CH₂—CH₃ 278.31  2 4-Quinolyl 363.37  3 —CH₂—CH₂—phenyl 340.38  4 4-Methoxy-3-methylphenyl 356.38  5 4-Trifluoromethoxyphenyl 396.32  6 2,4,6-Trimethylphenyl 354.40  7 4-tert-Butylphenyl 368.43  8 3,5-Dimethoxyphenyl 372.38  9 —CH₂—C(CH₃)₃ 306.36 10 4-Ethylphenyl 340.38 11 Thiophen-2-yl 317.34 12 —Phenyl—CO₂—CH₃ 370.36 13 4-Phenoxyphenyl 404.42 14 —C(CH₃)═CH—phenyl—C(CH₃)₃ 408.50 15 —CH₂—CH(CH₃)—phenyl 354.40 16 —CH(CH₃)—CH(CH₃)—C₂H₅ 320.39 17 2,5-Dimethyl-4-methoxyphenyl 370.40 18 3,5-Diohloro-2-hydroxyphenyl 397.21 19 3,4-(Methylenedioxy)-6-nitrophenyl 401.33 20 3,5-Dimethoxy-2-methylphenyl 386.40 21 3-Ethoxy-4-methoxyphenyl 386.40 22 3-Ethoxy-4-phenylphenyl 418.45 23 —Cl₂H₂₅ 404.55 24 2,3-Dimethyl-4-methoxyphenyl 370.40 25 3-Hydroxy-4-nitrophenyl 373.32 26 2-Ethoxy-3,5-dimethoxyphenyl 416.43 27 3-Bromo-2,4-dimethoxyphenyl 451.27 28 2,4-Dimethoxy-3-phenyl 386.40 29 4-N-(C₄H₉)₂—phenyl 439.55 30 3-Bromo-3-methoxyphenyl 421.25 31 9-Anthracenyl 412.44 32 2-Hydroxy-3,5-diiodophenyl 580.12 33 3-Bromo-6-hydroxy-5-methoxyphenyl 437.25

TABLE 5

Ex. R¹ Chem. mass  1 —CH₂—CH₂—CH₃ 380.44  2 4-Quinolyl 465.51  3 —CH₂—CH₂—phenyl 442.51  4 4-Methoxy-3-methylphenyl 458.51  5 4-Trifluoromethoxyphenyl 498.46  6 2,4,6-Trimethylphenyl 456.54  7 4-tert-Butylphenyl 470.57  8 3,5-Dimethoxyphenyl 474.51  9 —CH₂—C(CH₃)₃ 408.50 10 4-Ethylphenyl 442.51 11 Thiophen-2-yl 419.48 12 —Phenyl-CO₂—CH₃ 472.50 13 4-Phenoxyphenyl 506.56 14 —C(CH₃)═CH—phenyl—C(CH₃)₃ 510.63 15 —CH₂—CH(CH₃)—phenyl 456.54 16 —CH(CH₃)—CH(CH₃)—C₂H₅ 422.52 17 2,5-Dimethyl-4-methoxyphenyl 472.54 18 3,5-Dichloro-2-hydroxyphenyl 499.35 19 3,4-(Methylenedioxy)-6-nitrophenyl 503.47 20 3,5-Dimethoxy-2-methylphenyl 488.54 21 3-Ethoxy-4-methoxyphenyl 488.54 22 3-Ethoxy-4-phenylphenyl 520.59 23 —C₁₂H₂₅ 506.69 24 2,3-Dimethyl-4-methoxyphenyl 472.54 25 3-Hydroxy-4-nitrophenyl 475.46 26 2-Ethoxy-3,5-dimethoxyphenyl 518.57 27 3-Bromo-2,4-dimethoxyphenyl 553.41 28 2,4-Dimethoxy-3-phenyl 488.54 29 4-N-(C₄H₉)₂—phenyl 541.69 30 3-Bromo-3-methoxyphenyl 523.38 31 9-Anthracenyl 514.55 32 2-Hydroxy-3,5-diiodophenyl 682.25 33 3-Bromo-6-hydroxy-5-methoxyphenyl 539.38 

What is claimed is:
 1. A compound of the formula I

in which: R¹ is
 1. (C₁-C₁₄)-alkyl,
 2. (C₂-C₆)-alkenyl,
 3. (C₀-C₆)-alkyl-(C₃-C₁₀)-cycloalkyl-(C₀-C₆)-alkyl, where the alkyl moiety is unsubstituted or substituted by one or more OH groups,
 4. (C₀-C₆)-alkyl-(C₆-C₁₄)-aryl,
 5. (C₀-C₆)-alkyl-(C₃-C₉)-heteroaryl,
 6. (C₂-C₆)-alkenyl-(C₆-C₁₄)-aryl,
 7. (C₂-C₆)-alkenyl-(C₃-C₉)-heteroaryl,
 8. (C₁-C₆)-alkanoyl, or
 9. a radical as defined under 4., 5.,
 6. or 7., where the (C₆-C₁₄)-aryl or (C₃-C₉)-heteroaryl moiety is substituted by 1, 2 or 3 identical or different radicals selected from the group consisting of (C₁-C₁₀)-alkyl, carboxyl, amino, nitro, (C₁-C₄)-alkylamino, hydroxyl, (C₁-C₄)-alkoxy, where one to all hydrogen atoms can be replaced by fluorine atoms, (C₆-C₁₂)-aryloxy, halogen, cyano, di-(C₁-C₄)-alkylamino, carbamoyl, sulfamoyl and (C₁-C₄)-alkoxycarbonyl, or two adjacent radicals on the (C₆-C₁₂)-aryl ring together are alkylenedioxy; R² is hydrogen, (C₁-C₁₀)-alkyl, (C₀-C₆)-alkyl-(C₆-₁₂)-aryl or (C₀-C₆)-alkyl-(C₃-C₉)-heteroaryl, where the C₆-C₁₂-aryl or C₃-C₉-heteroaryl moiety is unsubstituted or substituted by 1, 2 or 3 identical or different radicals selected from the group consisting of carboxyl, amino, (C₁-C₄)-alkylamino, hydroxyl, (C₁-C₄)-alkoxy, halogen, cyano, di-(C₁-C₄)-alkylamino, carbamoyl, sulfamoyl and (C₁-C₄)-alkoxycarbonyl; R³ is —X—R⁴; X is —O—, —NR⁵— or —S—; R⁴ is defined as R¹;  or, alternatively to the definitions of R⁴ and R² above, R⁴ together with R² forms a bridge member —CH₂—CH₂— or —CH₂—CH₂—CH₂—; R⁵ is hydrogen or (C₁-C₆)-alkyl; A is a fused cyclic ring system which a) is substituted by one, two or three oxo or hydroxyl functions, where one hydroxyl or oxo function is in the neighboring position to the dihydropyran ring, and b) is mono, di- or polysubstituted by a (C₁-C₁₀)-alkyl radical or a carboxyl group, where at least one alkyl substituent carries a functional group; or a physiologically tolerable salt thereof.
 2. A compound as claimed in claim 1, wherein R¹ is as defined under 9, and the two adjacent radicals on the (C₆-C₁₂)-aryl ring together are methylenedioxy.
 3. A compound as claimed in claim 1, wherein A is a fused cyclic ring system which is substituted by one or two oxo or hydroxyl functions.
 4. A compound as claimed in claim 1, wherein A is a fused cyclic ring system which is mono- or disubstituted by a (C₁-C₁₀)-alkyl radical or a carboxyl group.
 5. A compound as claimed in claim 1, wherein A is a fused cyclic ring system that is mono- or di- or polysubstituted by a (C₁-C₁₀)-alkyl radical or a carboxyl group, where at least one alkyl substituent carries a hydroxyl, carboxyl, or amino group.
 6. A compound as claimed in claim 1, wherein A is a fused cyclic ring system which is mono, di- or polysubstituted by a (C₁-C₁₀)-alkyl radical or a carboxyl group, where at least one alkyl substituent carries a hydroxyl, carboxyl or amino group.
 7. A pharmaceutical composition comprising an effective amount of a compound as claimed in claim 1, together with a pharmaceutically suitable auxiliary.
 8. A method for the treatment of a metabolic disorder comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 9. A method as claimed in claim 7, wherein the metabolic disorder is diabetes or arteriosclerosis.
 10. A method for the treatment of a disorder of the cardiovascular system comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 11. A method for the treatment of a disorder of the central nervous system comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 12. A method for the treatment of a disorder of bone metabolism comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 13. A method for the treatment of cancer comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 14. A method for the treatment of an autoimmune disorder comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 15. A method for the treatment of infection comprising administering to a host in need of such treatment an effective amount of a compound as claimed in claim
 1. 16. A compound as claimed in claim 1, in which the fused cyclic ring system A is 1,3-pyrimidine, benzene, dioxane or cyclohexane.
 17. A compound as claimed in claim 1, in which the compound is a compound of formula

or a physiologically tolerable salt thereof.
 18. A compound as claimed in claim 1, in which the compound is a compound of the formula

or a physiologically tolerable salt thereof. 